3-(Trifluoromethyl)aniline → HCID 9924935, compound

HRID 1934909Notes

Reaction equation

HRID 1934909 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[F:17][C:18]([F:27])([F:26])[C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22].C(=O)(O)[O-].[Na+]>C(O)C>[N+:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:15]#[N:16])=[C:2]2[NH:22][C:21]1[CH:23]=[CH:24][CH:25]=[C:19]([C:18]([F:17])([F:26])[F:27])[CH:20]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 516892Sodium BicarbonateHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 9924935HCID 9924935, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 10.6 g (45.7 mmol) of 4-chloro-6-nitro-3-quinolinecarbonitrile and 8.82 g (54.8 mmol) of 3-(trifluoromethyl)aniline in 270 mL of ethanol was refluxed under N2 for 5 h. The reaction was diluted with ethanol, neutralized with satd sodium bicarbonate and evaporated. The residue was slurried with hexane, collected, washed with hexane and water and dried in vacuo (60° C.) to give 10.9 g of yellow solid. A 2.00 g sample was recrystallized from ethanol to give 1.20 g of bright yellow solid; mp 260-261° C.

Workup

  1. temperaturewas refluxed under N2 for 5 h
  2. customevaporated
  3. customcollected
  4. washwashed with hexane and water
  5. customdried in vacuo (60° C.)

Sources & evidence

ORD record
ord-d52bf3b2562d417a9890b86697d92a96
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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